Legendary investment manager and short-seller Jim Chanos confirmed unwinding a trade in which he was betting on the leading Bitcoin (BTC) treasury firm Strategy 's (Nasdaq: MSTR) premium to fall.
Chanos is best known as the founder of Kynikos Associates, a New York City-registered hedge fund focused on short selling.
In 2001, he famously nailed the prediction on Enron's collapse and eventual bankruptcy. Quick to identify overvalued companies, he has earned the reputation as Wall Street's most prominent short seller.
Related: Michael Saylor's MicroStrategy misses S&P 500, Robinhood to make unexpected entry
Highly critical of Michael Saylor-led Bitcoin treasury company, Chanos has often slammed the company's Bitcoin strategy as "ridiculous" and "too leveraged." He has also criticized its decision to pivot from solely accumulating Bitcoin to taking out debt to buy more Bitcoin.
Strategy's shares are worth a lot more than the Bitcoin they represent, Chanos has claimed time and again. The main financial indicator that he cites to slam Strategy is the multiple-to-net-asset-value (mNAV).
mNAV is a premium that measures how Strategy's stock price compares to the value of its Bitcoin holdings per share, minus debt and preferred equity.
Chanos has bet on Strategy's mNAV declining over time which means the company's stock value won't be much higher than Bitcoin each share.
In simple words, a Strategy shareholder is essentially seeking an indirect exposure to Bitcoin. But the company is offering this exposure at a high rate, he has contended.
On Nov. 8, the veteran short seller confirmed closing MSTR short and BTC long positions.
Strategy's mNAV has compressed from 2.5x in December 2024 to 1.23x in November 2025 and the compression is expected to continue over time and will eventually hit 1.0x, he added.
When the mNAV hits 1.0x, the company's shares will be valued exactly equal to its Bitcoin holdings. Anything below would be valuing Strategy less than its Bitcoin holdings.
More News:
Strategy issues preferred stock, skips common stock
Meanwhile, it has turned out that Strategy issued $50 million in preferred stock to acquire Bitcoin during the Nov. 3-9 week.
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10.00% Series A Perpetual Strife Preferred Stock (STRF): $16.6 million
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Variable Rate Series A Perpetual Stretch Preferred Stock (STRC): $26.2 million
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8.00% Series A Perpetual Strike Preferred Stock (STRK): $5.1 million
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10.00% Series A Perpetual Stride Preferred Stock (STRD): $1.3 million
The company is required to pay dividend payments on these offerings. Notably, it didn't sell any of the common MSTR shares, unlike previous times, for Bitcoin acquisition last week.
The company's valuation at $71 billion as compared to its Bitcoin holdings worth $67.8 billion translates to a 1.06x premium or mNAV — the lowest in 20 months.
The MSTR stock was exchanging hands at $240.75 at press time, down 0.55% in a day. Bitcoin, on the other hand, has jumped more than 2% in a day to trade at $105,851.41 at the time of writing.
This story was originally reported by TheStreet on Nov 10, 2025, where it first appeared in the Trading News & Analysis section. Add TheStreet as a Preferred Source by clicking here.
